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Synthetic method for 3,6-branched glucosepolyheptasaccharide

A synthesis method, glucose technology, applied in the field of synthesis of 3,6-position branched dextran heptasaccharide, can solve the problems of complex synthesis method of glucose oligosaccharides, unfavorable industrial production, low utilization rate of raw materials, etc., and achieve good self-defense immune system And the effect of regulating plant growth, high utilization rate of raw materials, and convenient operation

Pending Publication Date: 2018-11-30
江西艾立斯特生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The currently reported methods for the synthesis of glucose oligosaccharides are relatively complex, and the utilization rate of raw materials is low, which increases production costs and is not conducive to large-scale industrial production.

Method used

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  • Synthetic method for 3,6-branched glucosepolyheptasaccharide
  • Synthetic method for 3,6-branched glucosepolyheptasaccharide
  • Synthetic method for 3,6-branched glucosepolyheptasaccharide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Preparation of glucotriose donor:

[0020] 1) Dissolve 3.705g, 5mmol of benzoylglucose trichloroacetimidate in 30mL of dichloromethane to obtain solution A, and dissolve 0.735g, 2.5mmol of tert-butyldimethylsilyl-α-D-glucopyranose Dissolve in 15mL of dichloromethane to obtain solution B, mix B and A to obtain solution C, add 230μL, 2mmol of TMSOTf catalyst to C, and then add Molecular sieves, after reacting at 25°C for 4 hours, thin-layer chromatography analysis showed that the reaction was complete, filtered with suction, evaporated the solvent under reduced pressure, separated by column chromatography, and used ethyl acetate / cyclohexane (1 / 3) as eluent Rinse and collect the corresponding components to obtain pure trisaccharides with a yield of 91.3%;

[0021] 2) Dissolve 7.250g, 5mmol trisaccharide in 30mL DMF, heat to 70°C to completely dissolve the glucose, add 2.9mL, 3.5mmol pyridine, take out the flask and cool it to 25°C, place the flask in an ice bath, add dro...

Embodiment 2

[0027] Preparation of glucotetraose acceptor

[0028] 1) Dissolve 1.481g, 2mmol of benzoylglucose trichloroacetimidate in 10mL of dichloromethane to obtain solution a, and dissolve 0.588g, 2mmol of tert-butyldimethylsilyl-α-D-glucopyranose In 10mL of dichloromethane, to obtain solution b, 1.241g, 2mmol of 4,6-benzylidene-2,3-di-O-benzoylglucose trichloroacetimidate was dissolved in 10mL of dichloromethane, To obtain solution c, mix solution a, solution b, and solution c to obtain solution d, add 80 μ L, 0.70 mmol TMSOTf catalyst to solution d, add Molecular sieves, after reacting at 25°C for 3 hours, thin-layer chromatography analysis showed that the reaction was complete, filtered with suction, evaporated the solvent under reduced pressure, separated by column chromatography, and used ethyl acetate / cyclohexane (1 / 3) as eluent Rinse and collect the corresponding components to obtain pure trisaccharides with a yield of 89.7%.

[0029] 2) 1.330g, 1mmol trisaccharides were dis...

Embodiment 3

[0035] Synthesis of target compounds

[0036] 1) 3.377g, 2mmol glucotriose donor, 3.224g, 2mmol glucotetraose acceptor and Molecular sieves were dissolved in 50 mL of anhydrous dichloromethane, stirred under nitrogen protection for 1.5 h, then 50 μL, 0.44 mmol of TMSOTf catalyst was added dropwise, and reacted at 25 °C for 4.5 h, thin-layer chromatography analysis showed that the reaction was complete, suction filtered, and reduced pressure The solvent was evaporated, separated by column chromatography, washed with ethyl acetate / cyclohexane (1 / 1.8) as eluent, and the corresponding components were collected to obtain pure heptasaccharide with a yield of 79.6%.

[0037]2) Dissolve 6.276g, 2mmol heptasaccharide in 35mL, 1% hydrochloric acid-methanol solution, react at 25°C for 2-2.5h, thin-layer chromatography analysis shows that the reaction is complete, evaporate the solvent under reduced pressure, and separate by column chromatography , using ethyl acetate / cyclohexane (1 / 1.8...

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Abstract

The invention discloses a synthetic method for 3,6-branched glucosepolyheptasaccharide, and belongs to the technical field of natural product synthesis. The method comprises the following steps: glucose trichloroacetimidate is used as a glycosyl donor, tert-butyldimethylsilyl-alpha-D-glucopyranose is used as a glycosyl acceptor, coupling is performed, acid hydrolysis is performed, activation is performed to obtain a glucose trisaccharide donor, glucose trichloroacetimidate and 4,6-phenylmethylene-2,3-di-O-benzoylglucose trichloroacetimidate are used as glycosyl donors, tert-butyldimethylsilyl-alpha-D-glucopyranose is used as a glycosyl acceptor, coupling is performed, hydrolysis is performed, the obtained material is used as a glycosyl acceptor, 4,6-phenylmethylene-2,3-di-O-benzoylglucosetrichloroacetimidate is used as a glycosyl donor, coupling is performed, hydrolysis is performed to obtain a glucose tetrasaccharide acceptor, the glucose trisaccharide donor is coupled with the glucose tetrasaccharide acceptor to obtain heptasaccharide, deprotection is performed, and therefore the target product 3,6-branched glucosepolyheptasaccharide is obtained. The synthesis disclosed by the invention is convenient to operate, has a high utilization rate of the raw materials, and is a high-efficiency synthetic method.

Description

technical field [0001] The invention belongs to the technical field of natural product synthesis, and in particular relates to a synthesis method of 3,6-position branched heptaglucan. Background technique [0002] The main chain of glucose oligosaccharide is 1→6β linkage, and the side chain is 1→3β linkage. Glucose oligosaccharide is a new type of biopesticide, which can stimulate the plant immune system to achieve the purpose of disease prevention and pest control. It is not toxic in itself, but it can stimulate the plant to produce systemic acquired resistance, stimulate the immune mechanism inside the plant, and play a role To the purpose of disease resistance and disease prevention. Since glucose oligosaccharides have a very significant effect on activating the self-defense immune system of plants and regulating plant growth, and do not pollute the environment and are harmless to human health, they will surely replace pesticides and plant growth hormones, and change the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/02
CPCC08B37/0009
Inventor 朱玉亮
Owner 江西艾立斯特生物科技有限公司
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